N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

ID: ALA570425

PubChem CID: 45485995

Max Phase: Preclinical

Molecular Formula: C16H18N2O4S

Molecular Weight: 334.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(/C=C2\SC(=O)N(CCNC(C)=O)C2=O)cc1

Standard InChI:  InChI=1S/C16H18N2O4S/c1-3-22-13-6-4-12(5-7-13)10-14-15(20)18(16(21)23-14)9-8-17-11(2)19/h4-7,10H,3,8-9H2,1-2H3,(H,17,19)/b14-10-

Standard InChI Key:  OYUHAIFMHYISSY-UVTDQMKNSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   15.0027  -16.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0016  -16.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7164  -17.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -16.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4300  -16.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7146  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1429  -15.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8596  -16.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1059  -16.9232    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9309  -16.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1941  -16.1486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5307  -15.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4093  -17.6034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5382  -14.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9103  -15.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6230  -16.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3393  -15.7453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2868  -17.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5726  -16.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8578  -17.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3428  -14.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0590  -14.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6301  -14.5048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 10 13  2  0
  1  2  2  0
 12 14  2  0
  5  7  1  0
 11 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
  2 18  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 17 21  1  0
  5  6  2  0
 21 22  1  0
  9 10  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA570425

   (Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 334.40

Molecular Weight (Monoisotopic): 334.0987

AlogP: 2.26

#Rotatable Bonds: 6

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.29

CX LogD: 1.29

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: -1.83

References

1. Li Q, Al-Ayoubi A, Guo T, Zheng H, Sarkar A, Nguyen T, Eblen ST, Grant S, Kellogg GE, Zhang S..  (2009)  Structure-activity relationship (SAR) studies of 3-(2-amino-ethyl)-5-(4-ethoxy-benzylidene)-thiazolidine-2,4-dione: development of potential substrate-specific ERK1/2 inhibitors.,  19  (21): [PMID:19796943] [10.1016/j.bmcl.2009.09.057]

Source

Source(1):

• Scientific Literature